


Coming Back to the Very First Time

by Mesmeret



Category: Supernatural
Genre: Age Difference, Alternate Universe - Porn, Anal Sex, Ass to Mouth, BDSM, Becky is the queen of Pornography, Blow Jobs, Bottom Castiel, Bukkake, Butt Plugs, Cock Rings, Come Swallowing, Comeplay, Crossdressing, Crossdressing Castiel, Crossdressing Kink, Daddy Kink, Dean and Cas make a Porno, Dirty Talk, Felching, Flavored Lube, Fluff, Fluff and Smut, Happy Ending, I love creating porn titles, In Public, Japanese Rope Bondage, Light BDSM, Lingerie, Lube, M/M, Multi, Office Sex, Porn, Porn Star Dean Winchester, Pornstars, Retired Porn Star Dean Winchester, Roleplay, Sex Toys, Sexual Fantasy, Virgin Castiel, Virginity, Virginity Kink
Language: English
Status: Completed
Published: 2013-08-25
Updated: 2013-09-01
Packaged: 2017-12-24 13:55:43
Rating: Explicit
Warnings: Creator Chose Not To Use Archive Warnings
Chapters: 5
Words: 12,507
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/940762
Author URL: https://archiveofourown.org/users/Mesmeret/pseuds/Mesmeret
Summary: <blockquote class="userstuff">
              <p>Dean is 43 and retired from an illustrious porn career. He's still looking hot and gets the occasional request to make another porno. But he wasn't expecting that DVD of that sexy dark haired boy confessing how much Dean turned him on.</p><p> </p><p>A fic written based on <a href="http://www.subbycas.tumblr.com/">Subbycas'</a> prompt: pornstar!dean enjoying his retirement till he watches a video of twink!pornstar!cas and decides its time to come out of retirement so he can fuck that tight little ass.</p><p>Beta'd by <a href="http://www.ice-koroleva.tumblr.com/">IceFemme</a></p>
            </blockquote>





	1. A Taste

**Author's Note:**

  * For [](https://archiveofourown.org/gifts).



Dean Winchester was a man of simple pleasures. He loved living life in boxers and a bathrobe or less. And his career in the porn industry guaranteed it so well that he retired at 40 to live out his years comfortably, with all the time in the world. Now, he filled up his life with custom cars, classes at the community college, and sports. Everyone outside his close circle of people were shocked when he retired. He was in his prime as Bruce Kent, the handsome bisexual who started out as a timid bottom in gay porn.

By the time he was in his mid twenties, he was masculine without being a meathead. He caught the attention of a few companies who competed to sign him. Temptations, the company whose contract he chose, gave him a 3 million dollar contract for 12 films a year. They agreed to his terms of choosing the costars and sex acts while the writers and directors at Temptations would create the story line. He was happy renewing the contract year after year as the awards kept coming in. He made a few good friends and got to fulfill some awesome fantasies of his. He had a 20x15 foot poster of the groundbreaking film _King of Lesbos_ in his living room. It was a film that just had lesbian scenes of Charly Candi, Joanna Harlot, Ruby Diamond, and Megan Diamond playing castaways on a tropical island while the native, Bruce, was watching. Although women didn’t really do it for Dean, he could see the eroticism of watching four gorgeous women pleasuring each other on a beach with a setting sun behind them.

Nothing really led up to his retirement, though. There wasn’t anything that made him feel in danger or unhappy. He simply woke up one day and just didn’t want to pull his dick out in front of a camera. Dean talked to his agent, Gabriel, about it and Gabe started up the process of turning down new jobs. Becky and Chuck at Temptations were bummed to hear about Dean’s decision. Becky was looking forward to casting the story lines where Bruce Kent was in older authoritarian roles. They ended the contract amicably and sent out press releases to the fans and media about Bruce Kent going into retirement. His fans reacted from hurt to outrage but thankfully nothing too scary came of it.

Once the hubbub died down, Dean moved on with his life. He still stayed single with casual dates but after being so sex-centric for over two decades, he needed a break. Unfortunately, his front porch would always have a package or three each week from some porn studio hoping to coax him out of retirement. Most of the time, the packages were of crappy DVDs of terrified young porn stars. He couldn’t bear watching them. Dean would send those DVDs out to the organizations who helped porn workers get proper representation. It was the most he could do.

Sometimes there would be a diamond in the rough. A cute boy or a handsome man that Becky knew was Dean’s type. Those DVDs would go into his spank bank. Dean currently had a dozen DVDs on that shelf. All were audition solo pieces of the men in their rooms getting themselves off with their hands or toys. A few were shy while most were turned on by the exhibitionism.

By the third year of Dean’s retirement, the amount of DVDs sent to his house in Beverly Hills had dwindled drastically. His spank bank had 16 men and he was content with it.

Until that fall day when he got a package from Becky. There was a long winded letter from her that explained that it would be a one time deal and the DVD was of the guy, Jimi Cox, acting in his first high production film that was “FOR BRUCE’S EYES ONLY!!!” Dean raised a brow. Jimi Cox sounded like a run of the mill porno name. He tended to stay clear of those but if Becky was this enthusiastic but polite enough to not barge into Dean’s house and force him into this film, he might as well watch it.

He loosened his bathrobe once the DVD was whirring inside the player. Soon a slender pair of creamy legs in white lace appeared on the 80 inch TV as a decent soft piano soundtrack played. Dean let out a soft moan. He only ever confided his love for crossdressing men to Becky during a drunken holiday party. He thought she wouldn’t remember. She did and he was okay with it.

The camera zoomed out as those legs crossed and uncrossed themselves. Dean felt a small twitch in his groin as manicured fingers ran down the tights to the straps of some killer white designer shoes that belonged on a runway in Milan instead of a porno. The heels shown on the HD screen looked like they were ivory. Becky wasn’t holding back on the production value. As the shoes fell to the persian rug, the camera finally panned up to show more of this Jimi Cox. The hands on the screen were unbuttoning a sheer robin egg blue blouse that wasn’t hiding a lace bralette at all. Dean nearly pumped a fist in victory when the camera got a shot of Jimi’s jaw line and startling pink lips. Dean would’ve thought they were tinted with makeup but he could see that they were chapped and in desperate need to be wetted by his tongue. He watched them move into a slow smile as Jimi’s hands finished unbuttoning the blouse.

Finally the camera zoomed out completely to show messy black hair and blue eyes. Dean was now sold on the idea of doing a film with this beautiful creature. Jimi stood up to continue undressing. The blouse fell down to join the white shoes. Dean groaned seeing soft hints of a six pack and a black happy trail that connected the white lace panties to Jimi’s belly button. The music faded by the time Jimi took off the bralette. The pretty boy on the screen spoke in a voice that opposed his appearance, “Hello, Bruce. I’ve been a fan for long time. I remember being little and seeing that hot big man on those movie covers. The movies I wasn’t allowed to watch. Sometimes he would be in my dreams.”

As Jimi spoke, his hands wandered his body until his fingers were lazily teasing his nipples, “When I was a big boy, my parents left me home alone at twelve. I knew what to do. Mm, I put one of the videos in the DVD player and fell in love.”

Dean was stunned. He couldn’t tell if this was some world class writing or an actual confession from this stranger. It was really fucking hot that he was the cause of Jimi’s first wet dream. Dean started to jerk his cock to the rhythm of Jimi’s nipple teases.

“He- ah! He took that other man and woman and made them have sex for him. I would close my eyes and believe that he was praising me for being a good slut for him.” Jimi started rolling his hips at an angle so Dean could see his bulge in profile. Dean remembered which film Jimi was talking about. It was one of his first threesome films and first time doing a scene with a woman.

“For a whole year, all I prayed for was for Bruce to eat out my pussy. I was too afraid to fantasize him fucking me with that huge cock in my tiny ass,” Jimi let out a whine before leaving his now deep pink nipples to slip off the lace panties. As he rolled the fabric down, he also took off the stockings. He was truly naked now. Without the femme illusion, Jimi was more of a lean athletic type. And Dean was all in on how versatile Jimi’s appearance could be.

Jimi moved to bend over the bed as the camera zoomed in on the pale ass that didn’t show signs of being hairy or waxed. Dean had spent enough time in the industry to see that this was a rare find of genetics. He sped up his fist around his cock to a medium pace. He wanted to last until the end.

“Then, for my sixteenth birthday, I got my own computer. I learned so much. I learned how to do this while watching your videos,” Jimi purred as he squeezed his ass leaving red impressions before spreading his cheeks to reveal his hole that looked well prepared without being distorted. “I would sometimes just hold myself open and ready for you while listening to you fuck through my headphones.”

Dean had to squeeze himself tight from feeling the rush of a premature ejaculation starting to blare in the distance. This Jimi was getting to be too much despite the fact that he was only 5 minutes in.

“Most of the time, I would fuck myself open with my fingers. It took me a few months to learn that sex toys were available to filthy boys like me. As much as I wanted a Bruce Kent dildo, I only got a slim dildo.”

That only reminded Dean of getting his cock cast for the dildo line based off of his cock. His brother thought it was the funniest and craziest thing Dean ever did during his 22 years in porn. At least Dean never had to admit fucking himself with one of the Bruce silicone dildos. He told himself it was an educational experience and a damn good one too.

All thoughts died in his head when he saw one of those hands leave the screen to come back with a light blue silicone vibe. It was thin but very textured and Dean remembered using the three settings on Joanna Harlot during a film.

“I hope you like watching me fuck my pussy with my toy. I got this one after seeing _Erotic Experiments_. It’s so small but so strong and makes my hole tingle with all the bumps.” Jimi started rolling it around inside himself and Dean could hear the soft hum. He could tell Jimi was hitting his prostate because then the man would give a whine that sounded like he had been on the verge of orgasm for days. The desperation became contagious and Dean groaned aloud.

“Dean, I wish you were here to fuck me or even touch. Or I could touch you with my fingers or mouth. I’ve been getting off on only you since I knew what that good tingle meant. Please, please, please!” Jimi let out a groan as he came. The camera was able to get the perfect shot of his balls twitching and length bobbing in the air coming untouched onto the sheets. Dean went to town on his own cock. Jimi used his real name. What the fuck? His orgasm came quickly as he watched Jimi collapse onto his side with his cock still leaking a small pool of cum on his hip. Dean watched Jimi move the cum around on his body and take a few licks before pouting.

“I wish I was cleaning your cum off of me. Well, I hope you enjoyed this. Call Becky and ask for Cas,” The man blew a kiss at the camera and then Dean heard Chuck shout, “Cut!” To Dean’s surprise, Cas then fell back onto the sheets with a huge blush

“Was that acceptable? I kinda got wrapped into it. You’re so mean, Rebecca. Making me jerk off to the sex god.”

“C’mon, Castiel! He’s going to love this! I think he’ll love to have a piece of your cherry pie,” the blonde woman winked at the camera. _Sneaky Becky!_

“But he’s never done virgin porn! It’s been one of his clauses since the get go! I can’t go and lose it to just anyone though.” Cas pouted but then grabbed the towel a production assistant handed to him. He cleaned himself up before wrapping it around his waist.

“Nah, you’re one of a kind and who knows, maybe he’ll get super possessive over you and you’re stuck with him forever!” Becky giggled as Cas gasped at her. Dean smiled as he watched them walk off the set.

_Interesting._

 


	2. Let's talk about sex

It took Dean three days to decide that he would indeed take Becky up on that offer. He called up Gabe first to get him to negotiate that this would be a one and done deal with no wiggle room. If Dean found out he liked Jimi/Cas, then he would have to start up a consenting non performer relationship with the guy. That scared the living shit out of him. He never had the opportunity to do so and it was making him feel stupid.

After picking up Dean in his garish sports car, Gabe took them to Temptations Studios. Becky, Chuck, and Cas/Jimi were waiting in the conference room already. Becky got up quickly and ran over to hug Dean, “Brucey! You’re looking good! Didn’t go tubby on me!”

Dean laughed awkwardly as the petite blonde started pawing at his midsection and arms through his black Led Zeppelin t-shirt. He knew body image was everything for the industry but he still took it personally.

“Becky, please. He’s looking great, you shouldn’t hit him where it hurts,” Chuck sighed and pulled his handsy wife off of Dean before giving him a hug. “It’s great seeing you again. You really should come to golfing more often.”

“Yeah, yeah. I will have my Tuesday mornings back when I’m done with my biology course this term,” Dean patted Chuck’s back in the hug. Pulling away, Dean startled a little to see Cas/Jimi standing to the side of Chuck with an expression that seemed like he was memorizing Dean. Dean took the chance to check Cas/Jimi out as well. The dark haired man was about three inches shorter than Dean at 5'11". Dean enjoyed the light hints of cologne and the too uniform 5 o’clock shadow. The man must’ve spent a good few hours grooming himself to perfection. Dean looked down from the handsome face to the well fitting heather gray t-shirt and dark blue jeans. What made Dean smirk the most was the clash of birkenstocks and the Nascar belt buckle.  

“So, is it Cas or Jimi today?” Dean broke the moment of silence in the room.

“C-Castiel is my full name. But Cas is easier,” Cas blushed and looked away to the windows showing downtown Los Angeles.

“And Jimi when he’s super easy!” Becky giggled. “C’mon! Let’s get this negotiation over with so you two can fuck!”

“Bec, stop insinuating that my client is nothing but a sex machine. He has feelings too,” Gabe smirked at Becky who smirked back. Dean and Chuck were used to the pair’s theatrics when it came to contract negotiations. When Castiel wasn’t sneaking glances at Dean, he looked a bit uncomfortable with the short bickering blondes talking about how long Castiel could blow Dean.

Chuck did his usual thing of starting up small talk, “So, Cas here is also going to school.”

“Uh, yeah. I’m going to UCLA,” Castiel blushed before taking a drink of water from his metal water bottle. Dean enjoyed watching that pale throat swallowing a little too long. Chuck made a small cough that brought Dean out of his reverie.

“Oh, cool. I’m just taking a few courses at Santa Monica College. What are you majoring?” Dean asked while watching Castiel lean over to put away his water bottle in his messenger bag. It was one thing to see Cas on his HD TV, it was a whole other thing to be just a few feet away from the smooth milky skin giving him a peek a boo from that gray shirt. **Damn**.

“Uh, I’m majoring in English and minoring in business management,” Castiel noticed Dean’s line of sight and smoothed out his t-shirt. Dean let out a whine of loss. Castiel gasped softly hearing it and stared at Dean with wide eyes of disbelief. Chuck knew it was his cue to go get coffee from the break room. Becky and Gabriel were still haggling blow job and 69 scenes.

“So, could I ask you, um, if what you said in the video was true?” Dean couldn’t help but lean in closer to Castiel. “That I was the first to make you cum?”

Castiel blushed down to his neck and nodded while looking at Dean if that was acceptable.

“That you’re a virgin waiting for my cock?”

“Ah! How do you know?” Castiel tried to back away in his chair before looking at Becky with an expression of dawning realization. “The fucking camera was still on.”

Dean couldn’t help but laugh, “Yeah, it was. She’s sly like that.”

Castiel took a deep breath and looked at Dean with a startling seriousness, “Please, I know you have standards. I don’t want you to break them for just one video. I don’t want to mess anything up for you. But I’m 21 and can’t even touch another man’s cock or be intimate with a woman without thinking about you.”

Dean raised a brow at how sincere Castiel was speaking. But that small part of self hate in Dean couldn’t believe that there was someone in the world, a stranger, who would be celibate because of him. Castiel shifted in his seat waiting for Dean’s response.

“Huh, I don’t really know what to say, Cas. You don’t even really know who I am. You’ve only seen my professional self.”

“We could go out!” Castiel looked away blushing deeply as Becky and Gabriel stopped bickering to look at him.

“Oh! Temptations holds the rights to produce a film when they get married! Mark that down or Dean can only fuck Castiel while wearing a ball gag!” Becky floundered with a big grin.

“Fine! But they decide if it will be bareback or not. Now, to acceptable dirty talk,” Gabriel replied.

Dean turned back to Castiel, “I think drinks after filming is over. Sounds good?”

Castiel nodded as his eyes welled up with tears. Dean couldn’t help by lean all the way forward and wipe away the stray tear. He saw Castiel hold his breath and caught up in the moment, Dean kissed him on the lips.

Chuck came back with a sigh and five coffee cups. “I’m glad you love birds aren’t rushing into fucking quite yet. Save it for my camera please.”

Dean pulled away from those soft pink lips with a pout at Chuck. By the time the three men were halfway through their coffee and a discussion about golfing, Becky and Gabriel were ready to read out the contracts. The agreement was that as long as Temptations produced the films that Dean and Castiel starred in, the couple shared 60% of the profits from the films as well as receiving $50,000 up front for each film. Castiel was shocked when he heard that. Dean knew college life was a strain. He got into porn to pay for his brother’s law degree at Stanford after all. He held Castiel’s hand reassuringly when Becky told them that she estimated that the sales of the film would be in the millions due to hype and how sexy they were together. Castiel was shaking a little when Gabriel handed him the contract. Dean watched Castiel sign his full name before Dean signed his own under it.

“Okay! Expect a script mailed to each of you on Monday. Wardrobe will want you two to come by two hours before shooting in case they need to do last minute alterations. Becky and I are still arguing if Cas should wear crotchless panties. I say no.”

“I SAY YES! HIS COCK HAS THE PERFECT CURVE FOR THEM!” Becky’s face grew red as she waved her arms about. Dean was always disturbed by how gung ho Becky could be about porn. Castiel just looked down at his own crotch as if trying to imagine wearing the mentioned underwear. Chuck just sighed and continued talking, “Shooting will be Wednesday from 10 am to 4 pm. We will do photos first and then film the scenes. Please take care of hygiene and all that. Castiel, even though we are advertising this as virginity porn, I would like you to wear a plug to get your body accustomed to something larger than 1.5 inches around.”

Castiel blushed, “Oh, okay. Would a Bronco work? I, um, got one by accident.”

Chuck turned to Becky, “Bronco plug is one and three quarters, right?”

“Yeah, it’s pretty hefty. Start with your standard small plug for the weekend and then start playing with the Bronco. For the storyline, I’d love it if you don’t cum for a day or two before the shoot, Cas. But if it happens, no problem.”

Dean couldn’t deny getting hard from this conversation. Usually hearing his co-star’s pre shoot ordeals didn’t do anything for him. But the whole allure of Castiel getting ready to experience sex for the first time was arousing as fuck. Dean knew how much of a pleasurable struggle walking around with a Bronco in your ass was. And if Castiel wasn’t going to cum for two days before the shoot. Dean shifted awkwardly feeling his hard on filling his boxer briefs to the limit.

“And as for you old pro, we’ll style you once you get here. Just shower, wax, and exfoliate. This will be an HD shoot,” Chuck turned to Becky. “That’s it right?”

“Yep! Can’t wait to finish this script! This is gonna be so much fun!” Becky hugged her goodbyes before heading to her office full of posters and polaroids of naked people doing sordid acts.

Gabe offered Castiel a ride but Castiel told them that he biked to the office. Dean was impressed. That must’ve been at least an hour and a half. Gabe reacted as if Castiel walked barefoot to Temptations. After a few minutes of trying to get Castiel’s bike in the small sports car, the three were off. Once they got to Castiel’s apartment at Westwood Palm, Castiel kissed Dean goodbye as the man lifted the bike out of the convertible back seat. Dean knew he had a stupid smile on his face but he didn’t care.

“You two make me sicker than two Midori sours,” Gabe grumbled as they drove over to Dean’s place.

 


	3. The Build Up

Monday morning rolled by and Dean checked his email to find the script _Coming Back to the Very First Time_. It was going to be a major shoot with multiple locations. Dean couldn’t help but jerk off to it while moaning his lines. It was one of the best pieces Becky ever wrote. He quickly cleaned up the cum on his hip before heading out to get manscaped for Wednesday. He learned early on in his career to leave behind the erotism and just move on in his day to day life. He got trimmed and shaved by a quiet asian lady who he has been going to for 14 years and still doesn’t remember her name. The guilt always made him tip her 45%. During the drive back home, he couldn’t help but think about how Cas was faring with his prep.

****

Tuesday rolled by and Castiel was in agony. He took the prep suggestions seriously and wore a cock ring since the previous day. But when he saw the script said that he was to cum unexpectedly during the first kiss, he needed the physical restraint. He spent all Tuesday taking care of his body instead of going to classes. During his weekend grocery run, he splurged on some home spa kits as well as an enema kit. He was blushing until he was dizzy praying the self checkout station didn’t malfunction. Thankfully it went smoothly and he biked back to his apartment feeling like this was really happening to him. He was going to be having sex with Dean.

He floated back to the present where he was in his bathtub taking an oatmeal bath to ease the burn from getting his legs waxed that weekend. Next up on the list of things he needed to do was a self manicure and then it was time to coax the Bronco into himself. The medium sized plug in him was feeling surprisingly comfortable while in the bath. He still had the urge to jerk off, but that was ignored.

As the water cooled down, he got out slowly as the drain did its work. Kneeling on the plush rug in his small bedroom, he coaxed out the plug. He breathed steadily as his body ached at the sensation of loss. He moved his ass in circles to help with the tension. He remembered some of his lines he was suppose to say before Dean fucked him. Castiel felt a little foolish but he might as well rehearse.

“ _Ta_ _ke me, Bruce. I only want to know how you feel_ ,” Castiel took the large plug that was slick with lube and teased it around his hole.

“ _Don’t tease me. I want to know what it really feels like. I’m tired of being teased and treated fragile_ ,” Castiel whispered the lines needily as he tried to relax enough for the plug to sink into him. He bit his lip as he felt the silicone settle in. He laid there with his ass up for a few minutes. Occasionally he would clench and pretend he was clenching around Dean. He spent a half hour in total with the plug in before taking it out slowly. His ass ached from the stretch, but there was no tearing. He slowly got up to make himself supper. He planned to use the plug before bed and then tomorrow was going to be Wednesday.

****

Dean was excited. It was finally Wednesday! He woke up from a sweet wet dream of Castiel bouncing on his cock while in the backseat of one of Dean’s prized cars. He had to quickly stamp out the fire building in his groin. He needed to save his cum for the afternoon. He was getting on in age and could only cum twice a day at best. He rushed out of the house in his lucky jeans and sweatshirt. He knew breakfast would be provided at Temptations.

Sure enough, Becky was waiting for him with a cherry turnover and coffee for him. “Here, Hot Shot. Wardrobe has moved to the first floor. I’ll walk you there. Your gentle prince is already there. He is in need of some wise words and caresses.”

“Thanks, Becky. One of these days you’re going to tell me where you get these,” Dean moaned around the first bite of the flakey sweet pastry.

“I’m not going to ever do that. I would rather never see porn again instead of writing scenes where you need assistance to fuck twinks because of your fat ass,” Becky snarked. They went through the office portion of the building to the wardrobe department. Dean was impressed seeing that there were now four changing rooms. He remembered when Temptations was still a small set up where he and the girls had to do makeup on Chuck’s couch.

“You’re so mean sometimes, Becky,” Dean gave her his best pout as they walked into the nearest changing room. Castiel was there wearing a padded bra under a tight crop top. He looked like he had a decent pair of perky B cups. Dean snuck a look down to see that Castiel wasn’t wearing the crotchless panties that Chuck had mentioned. Instead, he was wearing a pair of lacy hip huggers in a soft pink. Dean could see the dark outline of a cock ring around the base of Castiel’s cock. Two of the stylists were arguing over three dresses oblivious to the aroused man in front of them. All were shades of soft pink but had different necklines and types of skirts. Castiel smiled shyly at Dean, “Hello, there. You’re lucky and just get to wear jeans and a t-shirt.”

“Ha! I will have you know that Dean’s outfit is $200 more than yours, Cas!” Becky walked over to the stylists and pointed at the shortest peach pink dress with floral lace and a matching pink belt. “[That one](http://www.modcloth.com/shop/dresses/talk-show-interview-dress), girls. Find a pink poppy pin in the accessories area with some black too. Do day makeup accordingly. And nude heels!”

Dean smirked as the two stylists whisked Cas out of the room. Poor kid. Dean sat down to his assigned seat and his stylist brought out the jeans, a comfortable t-shirt that had a design on it that wasn’t too douchey, and some super soft boxer briefs that were a deep chocolate brown. One of the perks of doing porn as a guy was the comfortable clothes. He felt a little guilty seeing Cas walk back into the room wearing heels and a queasy face. Dean leaned over to Castiel once he sat down, “You look perfect, Cas. You’re going to do awesome. Just stick to your lines. Until we’re at the apartment scene, we’re just actors.”

Castiel smiled back, “Thank you, Dean. I will do my best but it is all so new to me.”

“I thought you’ve done a few films?” Dean slipped his fingers between Cas’ trembling ones.

“Yeah, but they were all filmed in my bedroom with my webcam for a cam site. Becky saw them and requested I join Temptations. Then, well, I masturbated for you and now we’re here,” Cas blushed and then relaxed his face as the makeup artist started applying his makeup. Dean pondered the new information as his own artist painted his face. He started drifting back to his first film with other guys. He was so nervous and did throw up a few times before the camera started rolling. He had chewed two breath mints quickly and then played his role as the college freshman getting hazed. Although it was scary, it was also thrilling to speak those cheesy lines and jerk two guys off while on his knees.

Soon they were led to the photography room. Castiel was starting to get the hang of walking in heels once they were in place under the bright lights of the set. Dean smiled when he recognized the photographer, “Kevin! Damn, almost didn’t recognize you! I’m digging the facial hair.”

The tired looking photographer smiled back, “Thanks, I just got back to LA this morning from Miami. Had a photoshoot there for Ralph Lauren Eyewear yesterday.”

Dean pulled him into a big hug while Castiel wobbled a little against the sofa on the set. “That is so awesome, Kevin! You’re really making it! Cas, Kevin here dropped out of pre med at UCLA to become a photographer.”

“Wow, that is impressive and must’ve taken a lot of courage.”

“It was terrifying but I’m finally making it. Anyways, I want to get a few shots of you two flirting first. Then we’ll build up from there,” Kevin walked over to his camera and gave them a nod to start posing.

Dean loved doing photo sets. He liked the frozen chemistry you had to build with the camera and the co star. Castiel did seem a bit robotic in his posing. At first he would only look at the camera. “Hey, Cas. Look at me. Pretend the camera is a film camera.”

Castiel tilted his head towards Dean, “Like this?”

Dean couldn’t help but stare at the beautiful lines of Castiel’s neck as it tilted. After he heard the click of the camera go off twice, Dean rested a hand on Castiel’s shoulder and leaned in as if to kiss the shorter man. Castiel gave a surprised gasp and Kevin made a few happy sounds, “Yeah! Play up that innocence a little more, Castiel! Dean, get a little more in his space but be mindful of the lighting.”

Castiel had a flash of confusion on his face before making his expression even more doe eyed. Dean whispered, “You’re so cute, I wanna keep you in my pocket.”

Castiel responded with a giggle and leaned up to whisper into Dean’s ear, “I wouldn’t mind as long as I could spend some quality time with what’s next to your pocket.”

Dean gasped as he felt long fingers run down his crotch before slipping into his pocket. “Hey now, not yet. You’re the one who’ll be cumming in their pants, remember?”

“Oh, you’re british now?” Castiel quipped but it was lost on Dean. “Pants is a term for underwear in the UK.”

“Thanks, I’ll remember that.” Dean kissed along Castiel’s neck while looking at the camera. Cas was whining and digging short nails into Dean’s arm.

“Okay! I think that’s a wrap!” Kevin called out as he went over to the computer where Becky was grinning madly. Dean and Castiel shared a look before being ushered out of the building to the location of the opening scene of the actual porno. Dean reviewed his lines on the plush shuttle bus next to Castiel who was muttering his under his breath.

Once they were at the grocery store, Chuck frantically got off the bus talking a mile a minute to all of the crew that followed him. “We need to set up lights and three cameras in the produce section! Get the extras briefed on their roles! Harris! Mic up Dean and Cas! We only have three hours total here before the store goes back to business! We can do this!”

Dean grinned as his friend went from a timid anxious man to a strong director in a matter of minutes. Harris came over with two wireless mics and hid them in the men’s clothing before doing sound checks. Harris gave them a nod to head to the produce section. Castiel then started to shake and look around nervously.

“What’s wrong? Need to piss?” Dean asked with his best calming voice.

“Uh, kinda. I need to remove my cock ring,” Castiel whimpered with embarrassment. Dean forgot about that. Hot damn.

“Well, wait for them to finish doing light checks and when they want us, you can take it off then.”

“But, everyone will see my cock!” Castiel whispered with a pout before realizing what he said. “I meant that- well, you know-”

Dean couldn’t help that loud laugh that bubbled out of him. “Oh, man! Seriously? Maybe porn isn’t for you.”

“It might be. But it has got me here...” Castiel blushed. Dean nodded in understanding.

“Okay, gentlemen! You two are needed in front of the cameras!” Chuck called out by the row of bulk bins.

Castiel whimpered and looked around for a moment before taking a deep breath. Dean watched feeling his cock come alive as Castiel lifted up his dress and carefully pulled down his panties while a hiss. Dean stared at the blood filled cock that was twitching in the chilled air.

“Need a hand with that, Cas?” Dean managed to get out after a weak groan.

“Uh, yeah. Just nothing too much, please,” Castiel breathed out shakily. Dean squeezed the hot base and rolled off the strong silicone band off of Castiel’s shaft. Both of them moaned. Dean felt how desperate Castiel’s body was while Cas was trying to not cum from the large hand holding his cock. He took a few deep breathes before getting his control back.

“Okay, I’m ready. Thank you, Dean,” Castiel got his clothes back in order before walking to his mark. Dean walked to his own with a smile. Time to work his magic.

“Scene one, take one!”

 

 


	4. Let's Get Actin'

Castiel heard the clap and took a deep breath. _‘You can do this. She’s flirty and innocent, Cas. Just like you.’_ Feeling confident, he turned the corner to walk towards the camera looking at the dry goods on display. He picked out a small box of oatmeal and placed it in his shopping basket. “Hmm. Maybe some fruit, too,” he thought aloud in a surprisingly feminine version of his voice. It was a deep, sultry voice that he had been practicing for a while now. The second camera followed him to the banana display. He looked at a few bunches before picking a ripe bundle of four bananas. He turned to go to the apples when Dean started walking into the frame. Castiel bumped into him right on cue, “Oh! I am so sorry, sir! I’m so clumsy sometimes.”

“Hey, it’s no problem, gorgeous,” Dean gave him a charming smile as his hands lingered on Castiel’s shoulders from keeping the shorter man from falling over in those heels. Castiel blushed for the camera and looked down at the ground.

“Oh, my god! I made you drop your basket! So sorry! Um, let me get your things for you!” Cas bent down to pick up the boxes and plastic jars that fell out of the basket. Then he got down to his hands and knees to get an orange that was halfway under a display bin. The crew had placed it there before the scene so the third camera could get a perfect shot of the dress riding up his ass to reveal his panties.

Camera 2 was picking up Dean openly checking out Cas’ ass before looking around to see if anyone caught him. Once the coast was clear, he walked up to Cas so when the brunette was up on his knees, his head was just a little below Dean’s crotch if he was to look towards his shoulder.

“You’re a helpful little thing,” Dean said with a breathtaking smile and Castiel gasped. Want a hand up?” Dean purred as he brushed a small lock of Cas’ hair back behind his ear. Castiel leaned into the touch before looking up and resting a hand on Dean’s forearm.

“Please? Um, what’s your name by the way?” Castiel asked as Dean helped him up.

“Me? Oh, I’m Bruce. And you?” Dean pulled Cas to him once the man was stable standing up.

“I’m Jimi,” Castiel smiled shyly up at Dean before trying to pull away from the embrace. “Oh! Oh, my god! Are you? Are you Bruce Kent?”

“Yeah, I am,” Dean let go and looked apprehensive. “Is that okay? I know I have a reputation of being a gay porn star and all. I don’t want to scare a sweet thing like you away though. You are very pretty.”

Castiel took a moment to look around at the extras milling about acting as if they are all going about their day getting groceries. Then he looked back at Dean and started to seduce the older man. “You think I’m pretty?” His innocent smile turned into a sultry pout. “I think you’re handsome. You look amazing in person. Could I tell you a secret?”

Dean gave Cas a smirk, “Sure, I might share one of my own too.”

Castiel leaned up to whisper in Dean’s ear loud enough for the mic to pick up, “If you don’t want to fuck pretty girls like me, I wouldn’t mind watching you fuck a boy toy next to me instead.” Cas pulled away with a blush and picked up his basket. “I’m sorry, that was too bold of me. I should get going.”

Dean groaned, “No, don’t leave, beautiful. I wouldn’t mind fucking you any day of the week.“ He moved forward to pull Cas to him and kissed those glossy pink lips. Castiel moaned into the kiss and dropped his basket to the ground.

“C’mon, we’ll cause a scene, Jimi. Let’s get out of here,” Dean smirked and grabbed both of the shopping baskets.

“Cut!” Chuck called out. “Good going! Time to set up the cameras at the checkout! Quickly now! We’ve got 2 more hours! I want three PAs putting things back where they were in this area so we can be more efficient.”

“Wow, Chuck is like Jekyll and Hyde,” Castiel mused while sitting down with Dean on one of the benches in the cafe section of the grocery store.

“This is his domain,” Dean smiled. “He is pretty passionate about filming pornography. I think Becky is the only person more passionate about this than him.”

“Yeah, that sounds about right,” Cas fell silent as they watched Becky chatter away with Chuck as the camera crew set up the cameras in the new positions. “Um, so where will we be getting those drinks?”

Dean looked over at Cas’ face for a moment, “I’ve got a decent liquor cabinet at my place. I’ve never really been one to go to a bar that didn’t sell anything for more than $10. But you deserve much better. Are you a beer or wine guy? I still got some microbrews my brother sent me from his bike trip along the coastline in Washington. If wine is your thing, I got a bottle of a 2000 Bordeaux. Apparently it’s a world class wine. I dunno, like I said, I’m more of a dive bar drinker.”

Castiel smiled shyly, “I like Jack and Coke, to be honest. But microbrews fascinate me.”

Dean grinned, “I’m more of a straight Jack on the rocks kind of guy.”

Their laughter was interrupted by a PA letting them know it was time for the next scene. A wardrobe stylist touched up their makeup and hair before they got into place.

“Scene two, take one!”

They walked up to the line of three bored looking extras in line for the checkout. Dean groaned, “Why is there always just one checker working?”

Castiel shrugged, “To torture us, I guess?”

“Cut! Cas, your voice is too manly.”

Castiel blushed and apologized quickly as he moved to the starting spot. Dean rubbed his back, “It’s okay. As long as we don’t have to take fifteen takes, we’re good.”

Castiel nodded and took a deep breath. Dean nodded at Chuck.

“Scene two, take two!”

****

They walked up to the line of three bored looking extras in line for the checkout. Dean groaned, “Why is there always just one checker working?”

Castiel shrugged, “To torture us, I guess?”

Dean laughed on cue when he heard Cas’ feminine voice reply, “Such cruelty, but at least I’ve got you.”

Castiel gasped softly as camera two caught Dean squeezing his ass. Cas then leaned against Dean’s side as the hand continued to grope, “We are gonna get caught, Bruce.”

“C’mon Jimi. I bet you’re wet already,” Dean whispered before looking around. “No one is looking.”

Feeling Dean slap his ass, Castiel gasped and whined in frustration, “Oh, my god! You’re such a jerk, Bruce! At least treat me right.” Cas pulled Dean into a hard and showy kiss. Camera Three showed them kissing passionately while the extras in front of them moved up in the line as an extra grabbed the bags of their purchased goods towards the exit. Dean and Castiel pulled away to move up a few steps before going back to kissing.

“You make the best sounds, Jimi. Are you getting off on this, you dirty girl?” Dean used his best domineering voice.

“Yes! I’m so close to cumming! You’re better than any fantasy of mine, Bruce,” Castiel moaned quietly.

“I want you to cum in your panties, Jimi. Be my good girl and come from my kisses,” Dean kissed down Castiel’s neck before nipping at his pulse with a well timed squeeze of that cute ass.

Castiel felt his cock cum for the first time in days. He let out a moan of relief as his legs went weak. Dean held him up while whispering praise into Cas’ ear that the mics wouldn’t pick up. Dean knew how jarring your first filmed orgasm amongst other performers could be.

“Were you a good girl just now?”

“Yeah, I was your good girl, Bruce,” Castiel breathed out while resting his head on Dean’s shoulder. That orgasm was so intense that Castiel was feeling ready to sleep. He loved being supported by Dean they went through the line. Quickly they were up to check their things out.

“Looks like your girlfriend could use a nap, dude,” The actor playing the cashier spoke in a bored voice as if small talk was painful for him.

“Yes, she had a long morning,” Dean replied while paying for the groceries. Castiel just gave the actor a sleepy but pleased smile that Camera Three picked up. “Let’s get you home, Jimi.”

Camera Three zooms in on the cashier’s confused face after Dean and Cas walked out of frame. “Isn’t Jimi a dude’s name?”

“Cut! Great take everyone! Thank you Andy for getting those lines right on the first try! Now, we’ve got 45 minutes to leave no trace we were ever here! Then we’ll go back to the studio. Dean and Cas, Becky should have your lunches ready in the bus right now. Cas, you’re underwear must be uncomfortable. Don’t worry, Becky has a change of clothes waiting for you.”

The two actors nodded before heading out to the bus in the empty parking lot. Becky was nowhere to be seen but there was two white paper bags with each of their names written in cursive. Dean opened his to find a cobb salad with more meat than lettuce in it to his joy. Castiel opened his to find vegetable minestrone. After changing out of his cum filled panties, he joined Dean in eating

“Um, so you really are good at kissing,” Castiel mumbled with a deep blush as he stirred his soup to cool it off.

Dean looked up from his salad, “Well, I’ve been doing it for over 30 years. I wouldn’t be here if I couldn’t tongue tango.”

Cas snorted after taking a sip of his soup, “Tongue tango? Was that what they called it back in the times of the discotheques?”

Dean tried to respond to the jab but his brain and mouth weren't connecting. Castiel watched him as if he was the most entertaining jester there ever was. Then that large grin on Cas' face fell and he shrank back in his seat, "Was I good at kissing? I felt like I was too slobbery."

"No, not at all! You, um, I like kissing you,” Dean knew he was smiling dorkily. He couldn’t help it as the make out scene replayed in his head. The little noises Castiel made and how soft his lips were against Dean’s. His eyes shut as he licked his lower lip. Castiel saw this and couldn’t stop himself leaning over the small table and nipped at Dean’s lip.

Dean opened his eyes startled with the taste of tomato and spices that clouded Castiel’s taste as the surprise kiss deepened. Castiel moaned as Dean dug his fingers into his hair. The stupid poppy pin fell out of his hair from Dean’s eagerness to guide Cas over onto his lap. Castiel looked at Dean with a shy smile once he was in Dean’s lap, “Can I get you off or can you only come once a day?”

Dean growled as his mind went numb with desire, “I will take a viagra if necessary. I think you deserve some action off camera.”

“Really?” Castiel bit his lip and looked down at Dean’s crotch. “Could I try sucking you off? I- I’ve never had the chance to do that before with a guy.”

“Oh, shit, Cas! Keep talking like that and I will cum in my pants,” Dean squeezed himself as his body was roaring to orgasm. He never pegged himself to be a possessive fuck for a virgin, but damn. He really, really liked that those lips never knew a cock until his.

“But I am just being honest,” Castiel pouted. “Honesty is very necessary. I can’t lie to you.”

“Cas, please. We’ll talk about the more sentimental things in life once you’ve learned how to suck my dick.”

Castiel gasped as Dean unzipped his jeans and pulled out his hard on. Cas slipped to the ground never looking away from Dean’s cock. He hesitantly held it and looked up at Dean in amazement, “It’s so real.”

Dean was aware in the back of his mind that this was some monumental moment in Castiel’s life. The younger man was seeing and holding his object of desire for the first time ever. That object just happened to be Dean’s cock and Dean really needed that hand to move up and down. “Yeah, babe. It’s so real you can even put your mouth on it.”

Castiel moaned before wetting his lips. With both of his hands, he held the thick cock up and flatten his tongue against the vein below the crown and slowly wrapped his lips over the large tip. His eyes fluttered closed as he felt and tasted a drop of surprisingly yummy precum coat his tongue. He wanted more of that taste and started to suck Dean’s tip while his hands pumped the long length. Dean watched while feeling like Castiel was sucking the air from his lungs through his cock. Cas was clumsy but genuine. Dean had been spoiled by the porn industry to expect skilled blow jobs. Castiel was giving him a blow job that was sloppy but the passion was there. Dean felt like he was being worshiped by that mouth and fingers.

“‘M I doin’ gud?” Castiel slurred while nuzzling the base of Dean’s spit shined cock. Castiel looked up at Dean with lust drunk eyes.

“Yes, fuck, yes!” Dean couldn’t help but thrust his hips up as Castiel sucked down a good four inches into his mouth. “Fuck! Gonna cum soon.”

Castiel moaned around Dean and started bobbing his head. He found it interesting though it could be better. He took Dean’s hands and guided them to his head, “I want to taste your cum as you fuck it into my mouth.”

Dean felt the floor fall away from him once those words were in his head. He thrusted into that open mouth shallowly for a minute before daring to go deeper. They paused for a moment when Castiel coughed from the surprising sensation of something thick in his throat. Dean resumed the thrusts when Castiel gave him an open mouth smile. The older man couldn’t look away from those deep blue eyes. Castiel was in love with him and it made the blow job feel like Dean’s first ever. It was such a new concept to Dean to please someone as they pleased him without an audience.

Castiel was in awe by the expressions that flashed through Dean’s face. It looked like the man was having an internal monologue that was written by Shakespeare. Castiel brought him into the present by digging his manicured nails into the soft of Dean’s hips and moaned as wantonly. Cas was quickly rewarded with a richer version of Dean’s precum. He held Dean’s tip in his mouth as the cock continued to pulse shot after shot of cum. The tingly bittersweet taste made Castiel salivate and so by the time Dean pulled out, Castiel’s cheeks were puffed out a little with a small dribble of cum leaking from the corner of his mouth that was quickly wiped away before it could stain the dress. It was so sweet and innocent, Dean wished he could photograph it.

“C’mon, you can swallow. Or do I taste that bad?”

The younger man shook his head frantically before swallowing, “No! Your cum is delicious! I wanted it to last long.”

Dean moaned softly and pulled Cas into a tight embrace, “You gonna be okay until we get to the next part of the shoot?” Cas gave him a nod against his neck. “Okay, let’s finish lunch, sexy.”

**Notes for the Chapter:**

> Whew. This was a challenge to write! Next and possibly last portion will be a little easier... or not.


	5. The Finale of all Finales

**Summary for the Chapter:**

> Cas finally gets to experience sex and there's a happy ending.

**Notes for the Chapter:**

> Sorry for the delay! I am being treated for adrenal fatigue and it reared its ugly head this week.

As they were finishing up lunch, Becky and the wardrobe stylists came back into the bus. Becky sniffed the air, “Dean, will you need a little blue helper this afternoon?”

“Eh, I’m fine, Becky. Cas is my aphrodisiac of choice,” Dean smirked at Cas. “Are we heading back to the studio now?”

“Yep. You two will shower and then it’s showtime!” Becky waved her best jazz hands before sitting down at her bench seat. The pair of stylists helped the pair of men change into loungewear before hanging up the designer clothes. Once the last crew members settled in, the bus driver pulled out of the grocery store parking lot. Castiel was secretly thankful it wasn’t his usual store. Nothing like an awkward boner in public.

Cas’ nerves were trying hard to set in but Dean was rubbing his neck in soothing circles. Cas looked up at him with a small smile and rested his head against the older man’s shoulder. Dean blushed once he noticed that Castiel had started to snuffle sleepily. They were still ten minutes away from the studio so he held the man to his side. Becky would sneak glances over the aisle and smile fondly.

Castiel was shaken lightly once the bus parked by the studio side entrance. He blushed deeply and stumbled up to his feet. Dean stood up quickly to help Cas with his balance, “Whoa there, colt. Let’s get you to the showers.”

Cas whined softly as they walked quickly to the showers, “I’m kinda scared, Dean.”

“Yeah, I was shaking more than a chihuahua in a snowstorm during my first time bottoming,” Dean shook his head. The real thing scared him so much, he was convinced he was going to tear something.

“C-could you, um, possibly join me in the shower? You’re so experienced and um, I’ve only done slim toys,” Castiel looked up at Dean uncertainly. He was preparing himself to be turned down. And it would be okay, really. He could be a man and get through the prep himself. He could do it.

“Oh, Cas,” Dean moaned his name and opened the door with the sign “Private Shower”. “After you.”

Castiel nodded shyly, “Thank you, Dean. This means so much to me.”

Dean kissed his cheek before getting undressed, “You mean a bit to me, too.” Cas touched his cheek with a dreamy look in his eyes. This was going better than he could ever imagine. Dean turned on the shower with a gasp as water started raining down from the ceiling and shooting from the walls, “What the fuck?! Everything here is different!”

Castiel laughed as he took off his clothes. He stepped into the spray and couldn’t resist leaning into the warm back in front of him. He ghosted his fingers along the paths of water rivulets that were working their way down Dean’s torso. Dean shuddered from a moment from the broad contact of skin on skin. One of his favorite fetish films he shot was him being a piece of human furniture for a pretty porn starlet to lay on and read fashion magazines on. He wouldn’t mind being Cas’ chaise in the future.

Cas stood on his toes to whisper in Dean’s ear, “What should I do now?”

Dean was brought back to the present and pulled out a washcloth and bodywash, “Be a good boy and let me clean you.”

Castiel nodded and let Dean wash his body. It felt soothing to let someone else do it, especially when it was Dean. Cas moaned softly as Dean’s cloth covered hand went over his crack and bumped the handle of the plug Cas had been wearing all day.

“Fuck, Cas. I can’t believe how awesome you are,” Dean moaned. He gently twisted the plug for a moment. After only hearing pleasured whines, he pulled it out slowly. It was a decent sized plug and looked clean. In the heat of the moment, Dean turned to face Cas’ blissed out face. He remembered that the man agreed to ass to mouth in the contract.

“Suck, baby boy. Gotta clean your toys, too,” Dean spoke with a lust drunk voice. Cas held the wrist of Dean’s hand holding the plug with both of his hands. The water had made Cas’ hair turn a deep onyx that only made his blue eyes stand out more as they stared at Dean eagerly. Dean stared back as that pink mouth panted against the plug before sucking it past those lips. Dean groaned deeply and pulled the plug away and placed it on the shower ledge.

Castiel whimpered as Dean nibbled his ear as his tanned hands kneaded Cas’ ass. Then two fingers tested the stretch of Cas’ rim. He whined as they went away instead of breaching his hole.

“I saw one of those lube shooters here somewhere,” Dean muttered as he looked through the basket on the shower ledge. “Ha! Here we go. You cool with cherry flavored lube? They got the clear cherry vanilla.”

Dean popped open the cap and squeezed a little on a fingertip before rubbing it against his lips. He puckered his lips at Cas and the younger man giggled but leaned up to lick them. “Mm, I like that flavor, Dean.”

“Cool, gonna eat you out with this,” Dean chuckled. He grabbed one of the lube shooters before filling it with the cherry vanilla lube. “Kay, baby boy. Spread your legs a little for me?”

Cas followed Dean’s orders and moaned at the sensation of room temperature lube filling his ass. He couldn’t wait for Dean’s hot cum in his ass. Castiel screamed silently as three of Dean’s fingers moved the lube around inside of him.

“One more and you’re gonna be my wet little girl, aren’t ya?” Dean purred into his neck.

“Yes, yes! I’m your wet fuck toy! I’m ready for your cock! Fuck!” Cas hissed as Dean squeezed the base of his cock and pushed the plug back in to hold all of the fresh, sweet lube in.

“Good, but you have to wait a little more,” Dean spoke hotly against his ear before turning off the shower. They both were silently catching their breath as they dried off. They didn’t really talk unless Becky or one of the stylists were asking them something. Dean would glance at Castiel and see that the man was in a fragile headspace. He wanted to take Cas to a nice place and make love. Dean wasn’t going to be infatuated with Castiel for a fleeting moment. Dean was already fantasizing what their 40th night together was going to be like. He blushed as Castiel smiled at him when the younger man caught him staring.

Once they were both dressed back up in the clothes from earlier and Cas was wearing panties that were soiled with sweet fake cum, they were led to the set. It was a complex set with a small living room connecting to a bedroom. The design team must have had a field day creating what Bruce Kent’s bachelor pad would look like. There were a few posters of Bruce’s more famous works and similar black and silver walls that Dean’s place had. Castiel looked at the whole set in awe.

“Okay, Cas, your marks are in red while Dean’s are in blue,” Chuck spoke from behind them. He ignored their startled murmurs, “We are aware you guys are beyond ready to fuck. So don’t fuck up your lines. You haven’t so far. Cas, women’s voice until your cock is out!” Chuck walked back to his chair.

Dean and Cas did a few quick walk throughs before Cas was panting softly, “We need to start, Dean.”

“Okay, Jimi,” Dean gave him a light kiss as they moved to the outside of the apartment door. An assistant was already there to grab the plug Cas was wearing. Cas squirmed for a moment trying to get used to the emptiness.

Then the  loud ring of the soundstage bell went off.

“Scene three, take one!”

****

“Sorry if it’s messy, beautiful,” Dean spoke once the door was opened. Camera one turned from facing the pair to take in the apartment space as the pair walked in. Dean set down the bags of groceries on the small dining table.

“It’s cozy. But sexy,” Cas internal cheered as his smokey feminine voice came out on the first try. He ran his fingers against the glass cover of a large poster of Dean in a preacher outfit fisting the hair of a brunette as he’s fucking her into orgasm. “I like the posters. I wish I was Lisa Brea in Fuck Me Father, I Have Sinned.”

Dean pressed Cas against the wall so Camera two can pick up Dean lazily grinding his denim clad hips into Cas’ pink lace covered ass. “We could always have a private retelling. But right now, I want to eat out your pussy and sink my cock into you, gorgeous.”

Cas played up his moans as he arched his ass up so he could feel Dean’s bulge against his crack, “Yeah, Bruce. I wanna do that. Where’s your bedroom?”

“C’mon,” Dean pulled Cas up into his arms. He managed not to grunt as he carried the smaller but firm man into the next room. Cas giggled and wrapped his arms around Dean’s neck and left pink kiss marks against his neck. Dean let out a soft groan as he laid Cas down on the bed before grinding against him.

Castiel moaned arching his hips up, “Fuck me, Bruce! I’m so wet!”

“Shh, I need to taste you first, Jimi,” Dean purred as he pushed up Cas’ dress to reveal the younger man’s bulge under soft pink lace hip huggers. “Oh, fuck, Jimi! Aren’t you a pretty thing. And a naughty little liar, too! You didn’t tell me you had a pretty cock, baby boy.”

Cas played up his innocence by trying to close his legs to cover his cock. But Dean’s strong hands held his legs open for a moment as he nuzzled Cas’ inner leg. Castiel moaned and begged in his real voice, “I’m sorry, Bruce! I am a naughty boy who likes being pretty girl. Please don’t hurt me, sir! Please! I just want your cock!”

Dean spread his legs wider after tugging down the lace underwear, “Don’t worry, baby boy. I prefer the taste of a cute cock and ass.” He then licked from Cas’ lube leaking hole up to the crown of his cock. Dean hummed around the Castiel’s tip before popping off in the most salacious way. “So sweet. I could get addicted, baby boy.”

“B-bruce! Please! Fuck my hole!” Castiel’s chest was heaving from the sensations. This was the first time he ever got his dick sucked and it was beyond perfect. Probably because Dean was perfect. He whimpered as the lines he memorized nearly disappeared when he felt Dean suck and nibble around his rim.

“Not yet, Jimi. Let Daddy taste,” Dean stabbed his tongue into Cas and wiggled it around groaning as the muscle spasmed against his own. “I gotta see how good your cum tastes, baby boy.”

Cas was writhing about trying to pull off the constricting dress. Dean paused for a moment to help him out of it. They shared a deep kiss. As Dean pulled back, Cas whimpered softly, “Can I tell you a secret, Bruce?”

“Sure, Jimi. What is it?” Dean rubbed his sides before playing with his nipples.

“Ung, I- ah! I’m a virgin! Oh, Bruce!” Castiel arched into the soft tugs of Dean’s fingers.

“Oh, fuck. Daddy will treat you right, baby boy,” Dean groaned as he leaned down to suck Cas’ right nipple and stroke his own cock slowly. Camera Three got the shot in profile and captured the moment where Cas’ cock bobbed and squirted a little precum onto Dean’s cock and hand.

Becky quietly gave Chuck the thumbs up.

“Thank you, Bru-Daddy,” Castiel blushed. Dean guided him to his hands and knees. Once in position, Dean knelt behind him and sucked on his left middle finger. With a soft pop, the finger left Dean’s mouth and slipped smoothly into Cas’ prepped hole. Castiel moaned and arched his ass up for more.

“Oh, you really do need Daddy’s cock, don’t you?” Dean groaned as he slipped in his pointer finger after a few pumps. Castiel dug his fingers into the dark gray bedding and keened desperately.

“Take me, Bruce. I only want to know how you feel,” Castiel growled his lines. “Don’t tease me. I want to know what it really feels like. I’m tired of being teased and treated fragile”

“Fine, Jimi. I’m going to fuck your virgin ass into this mattress,” Dean leaned over Cas’ body to growl into his ear. He ground his cock hard against Castiel’s ass, nearly slipping in.

“Please! Just do it already! Now!” Cas broke character and humped back as he slipped his hands back into Dean’s hair and tugged the older man into a harsh kiss. Dean slapped his ass lightly which caused Cas to gasp into the kiss and drop his hands from Dean’s scalp. Dean growled and lined his cock up to the spasming hole.

“Are you sure? Last time before this is final, Jimi,” Dean panted the line while looking at Cas’ glare.

“Fuck me before I fuck you, Bruce,” Castiel growled. His threat was rewarded with feeling his whole body getting split apart and fused whole at the same time. He scrambled blindly for Dean’s hand to ground himself from the terrifying pleasure pain. Dean could feel the turmoil under the pale back before him. He knew he was breaking character when he slowly pulled Cas to him as he shifted to his right side.

“Shh, it’s okay, Jimi. Let’s not rush things,” Dean spoke softly as he stroke Cas’ softening cock lazily with his left hand. “You’re so beautiful taking me deep in you. All eight inches of me in your first go. Such a good boy.”

Castiel finally started breathing deeply as the burn died off. The new position felt amazing. He cautiously started to roll his hips once he felt the burn to move. Dean moaned soft encouragements as Cas moved. Castiel leaned his head back against Dean’s and wove the fingers of his left hand between Dean’s to thrust his cock through. Both of them started moaning in unison as Cas kept up a steady pace. Dean nuzzled his pulse and pulled back a minute later to reveal a bright purple love bite to Camera Four.

“Oh! Mark me more, Bruce! Wanna be yours!” Dean started to thrust into Castiel hard and nibbled marks along the pale shoulder. He was rewarded with Castiel’s ass spasming erratically around him.

“Close, Jimi. Can I cum in you? I’ll lick you clean after,” Dean grunted as he thrusted hard and deep.

“Yes! I wanna feel your cum drip down my thighs like a filthy cumslut,” Castiel panted. His brain was too lust addled to say the right lines. He just admitted his darkest wish in front of four cameras and he didn’t care.

“Oh, baby boy! Are you going to be Daddy’s filthy cumslut?” Dean was blown away by Cas’ admission, but ran with it like it was an Olympic sprint. “Gonna mark your cute hole after I eat out my cum. You’re only going to cum once your mouth is full of cum and I am sinking my teeth in your cute taint.”

Castiel arched and keened pathetically as Dean squeezed the base of his cock hard. Cas felt his sanity slipping away as he felt Dean’s cum fill him while his own orgasm was denied. His body twitched involuntarily as Dean moved his body back to hands and knees for the cameras to get his clenching hole in perfect view. Dean moaned as the creamy white of his cum started to push out of the puffy rim. He licked the trail of his cum off of Cas’ balls before it tried to drip down onto the sheets. Keeping it in his mouth, he sucked more of his cum from Cas’ body.

The man beneath him was whimpering and panting nonsense while weakly clenching the sheets in his fists. During some of the harder and noisier sucks, Castiel tried to fuck the air but Dean held his hips still with a firm touch. Finally, Castiel was flipped onto his back and Dean kept his mouth open and slowly let his cum fall into Cas’ panting lips. Cas managed to keep his mouth open and not swallow. His breath became more harsh through his nose once Dean slid back down between his legs.

“I bite, then you swallow and cum. Got it?” Dean purred when Cas gave him a weak nod. Dean lifted Cas’ balls up to show the cute skin between his heavy sack and his spasming asshole. With a passionate groan, Dean leaned forward and bit down on the erogenous zone.

Castiel screamed before he could finish swallowing. It felt like he was tased with lethal pleasure. He dimly remember feeling his stomach getting wet from his cum as the world went black.

Dean moaned at the sight of Cas’ subconscious taking over. The young man’s cock was still twitching and coating the pale abdomen with creamy cum. Dean leaned forward and lapped up the cum with soft moans. By the time he was about to clean Cas’ cock, Castiel was coming to.

“Oh, Dean. That as so amazing,” Castiel blushed deeply realizing he said Dean’s name. But no one called out to end the scene. Instead, Dean looked up at him with a soft smile.

“I thought it was more awesome than amazing,” Dean moved up to kiss him tenderly. Castiel mewled into the kiss and clung to the older man. The loving affection was driving Castiel crazy. He needed to return it. He needed to express it. “I love you, Dean.”

“Love you too,” Dean mumbled shyly. He hoped it wouldn’t be picked up by the mics, but after hearing the quiet commotion by the director’s chair, it was.

Castiel moaned softly, “Cut!”

****

Becky rushed over with a huge grin and jumped into the bed to hug the naked men, “Congrats! That was so sweet and precious!”

Chuck sprinted over to pull his wife away along with one of the sound guys, “Rebecca! Workplace harassment!!! What were you thinking?!” He glared at the enthusiastic blonde before turning to the pair on the bed who were slipping on the robes offered by a production assistant. “Great job, you two. Whenever you have a hankering for a sequel, call us.”

Castiel blushed deeply, “Don’t we have to reshoot the end? I ruined so many lines.”

Both Becky and Chuck shook their heads. Becky spoke up, “Not at all, Cas! It was so perfect and sexy! You two should go get those drinks and have a sleepover.”

Dean kissed Castiel’s temple, “Let’s have a threesome with JD and watch some Die Hard?”

Castiel nodded with a small yawn, “After a nap. Sex is exhausting.”

********  
  


**Five Years Later**

Dean and Castiel were at their third AVN award ceremony together. _Coming Back to the Very First Time_ became the most sold gay porn overnight. Especially with the handheld and CCTV camera work woven in. Turns out Becky and Chuck had placed cameras on the bus and in the shower along with mics. The film was the triple threat of amateur, professional, and just plain taboo. The media became enraptured by the couple once they discovered that Dean Winchester was Castiel Novak’s first and only crush.

The success enabled Castiel to take as many college classes as he wished and settle in with Dean as a stay at home writer. He was able to indulge writing gritty horror and suspense novels that became cult classics.

It was two years after their first video was published when Cas brought up the idea for the second film. Dean listened to the idea and spent a few days debating on whether he was comfortable enough to let the world see Cas again. He was aware his love had been labeled as a sissy boy and a bottom. But over the months of dating, they learned they were comfortable switches. On the third day of contemplation, Dean agreed and they called Becky up with the idea.

Their second film, _The Discipline of the Hunter_ , was based off of a fanfiction story Becky wrote in secret when Castiel showed her the first manuscript of his novel. It started with Dean driving down a road when his classic car broke down. A stranger, Cas, gets out of his own car with a domineering swagger. Cas offers to help for a price. The viewers were shocked to see Jimi Cox go from sweet and innocent to a masculine top. But no one was complaining.

Another two years later, it was Dean who suggested doing a third film. He knew he was nearing fifty, but he felt like he still had something more to give. Castiel didn’t wait even an hour to tell him yes. It was a simple film where Dean was a business executive and Cas was hired to service him. Cas filmed going up the elevator in one of the skyscrapers of San Francisco and was led to Dean’s office by his secretary to be restrained in rope bondage and hung up on the coat rack in the corner of the office. Once Dean came back from a meeting, he unhooked Castiel and fucked his throat. Cas was left there wanting more as Dean carried on with his day. The next few scenes were similar but then there was the finale.

Dean’s boss walks in to find Dean fucking Cas tied to the ceiling. The boss holds a meeting of all of the executives and lectures how shameful and selfish Dean was to hide such a pretty slave. Dean is then stripped down and tied up like Castiel and both are forced to make out while being cummed on by 23 men.  

And so here they are now, Dean in a suit and Cas wearing a smattering of tasteful gems to cover his own as they walk along the red carpet. They cheekily pose with their hands out to show the photographers their engagement rings. Dean gave Cas a stunning vintage diamond and aquamarine ring and to not be outdone, Castiel tracked down the ring of Ed Cole, one of Chevrolet’s key designers of Dean’s favorite cars. It was a simple and masculine ring that only the two of them needed to know the importance of.

That night, their film, _Executive Decisions_ , won them and Temptations six out of ten nominations. Dean sighs to Castiel once they are back home in their pjs, “I think I’m finally ready to retire.”

Castiel kisses him gently, “Good. So am I. I think we should get a house in the French Riviera and learn the language as the days go by.”

Dean pulls him close, “Sounds good, my love.”

**Notes for the Chapter:**

> OMFG. I love creating porn titles. So much fun!  
> And yeah, I might've fantasized once or twice of Dean and Cas being the center of a bukkake scene... or of Cas being like Misha's character in Par 6 and taking in the city boy and showing him what's what.  
> Much love to all of you and I hope this was an enjoyable read. Longest one shot I've ever done!  
> Next up... CATBOY UNIVERSE! But I have finals during the next few weeks for school. Follow me on [Tumblr](http://www.mesmeretmarjorie.tumblr.com) for updates, small drabbles, and my daily rambles.


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